A Home Run Derby winner, 2011 Home Run Derby winner
The clues: The Dominican baseball player was drafted by a legendary team in 2005 and is known as one of its best postseason players today.

Who's flashing this smile?

Alberto Callaspo

A longtime bachelor, "Ides of March" Clooney
The clues: The former TV star and Oscar winner – who makes his home in an Italian villa – has been spotted with a new lady friend on his arm.

Who's flashing this smile?

George Clooney

talia balsam, george clooney stacy keibler,

Acquitted of murder in Italy,
The clues: The Seattle native was studying abroad when her roommate was sexually assaulted, murdered and left for dead. Her conviction was overturned this week after four years in jail.

Who's flashing this smile?

Amanda Knox

meredith kercher,

A late-night funny man, "The Late Show" host
The clues: The native Indianan has endured hosting feuds, a troubled stalker and even a sex scandal during his decades-long television career.

Who's flashing this smile?

David Letterman

david letterman jay leno, david letterman stalker, david letterman blackmailer

A music icon, "Like a Virgin" singer
The clues: Her nearly 30-year-long music career has included brief forays into acting, directing and now a fashion line with her daughter.

Who's flashing this smile?

Madonna

madonna everybody, lourdes fashion line, madonna super bowl,

A sidelined quarterback, Indianapolis Colts quarterback
The clues: He comes from a legendary football family and won a Super Bowl ring, but now finds himself in an unexpected role due to an injury.

A 'Dancing' star, Dancing With the Stars war veteran
The clues: The war veteran, who sustained severe burns during a tour of Iraq, is now a reality TV and soap opera star who is blowing away judges with his dancing skills on "Dancing With the Stars."

Who's flashing this smile?

J.R. Martinez

J.R. Martinez all my children, dancing with the stars, J.R. Martinez war tribute

A history-making first lady, First lady of the United States
The clues: The Princeton alumna didn't meet her future husband until they worked at the same law firm despite attending the same Ivy League law school.

Who's flashing this smile?

Michelle Obama

jason wu michelle obama

A young Oscar winner, Sookie on True Blood
The clues: This star of a sexy, gory and popular HBO series -- who married her co-star last year – first became famous at the tender age of 11 when she won an Academy Award. Watch her acceptance speech.

Top-ranked male tennis player, Armani underwear model tennis player
The clues: He's currently the No. 2-ranked male tennis player in the world, behind a Serbian player. This tennis player has also added underwear model to his list of accomplishments.

Who's flashing this smile?

Rafael Nadal

A royal newlywed, Duke of Cambridge
The clues: The 29-year-old prince was one of the world's most eligible bachelors until he married a commoner in an extravagant ceremony earlier this year.

Who's flashing this smile?

Prince William

prince william PETA

A former secretary of state, Former secretary of state Stanford professor
The clues: The classically trained pianist made history as the first female African-American secretary of state. Watch her swearing-in ceremony.

Who's flashing this smile?

Condoleezza Rice

u.s. secretaries of state list, condoleezza rice stanford professor of Political Economy, Condoleezza Rice dick cheney,

An Oscar-winning A-lister, "Pretty Woman" actress
The clues: The auburn-haired leading lady – known for her infectious laugh – was nominated twice before finally winning an Academy Award for this 2000 movie.

A Super Bowl-winning QB, Green Bay Packers quarterback
The clues: He's one of the highest-rated quarterbacks in the NFL. Before winning the Super Bowl in February, he had backed up another QB great.

Who's flashing this smile?

Aaron Rodgers

Aaron Rodgers the Championship Belt,

An NFL QB, New York Jets quarterback
The clues: He was drafted by the NFL in 2009 as the No. 5 overall pick from a California football powerhouse.

Who's flashing this smile?

Mark Sanchez

mark sanchez 2010 tony awards, Mark Sanchez GQ,

A Wimbledon champ, Women's three-time Grand Slam winner
The clues: The three-time Grand Slam winner is famous for her vocal playing style as well as her fashionable on-court attire.

Who's flashing this smile?

Maria Sharapova

A 'Dancing' goalie, 2011 Women's World Cup
The clues: She helped the U.S. women's team get into the final match of the 2011 World Cup before joining Season 13 of "Dancing With the Stars."

Who's flashing this smile?

Hope Solo

2011 women's world cup final, dancing with the stars,

A world-famous astrophysicist, Director of Hayden Planetarium
The clues: He's the director of a world-renowned New York City planetarium, host of a PBS series and a radio show and will soon take on a reboot of a late astronomer's popular TV series.

A first-time Senate candidate, Harvard law professor Senate candidate
The clues: Before running for Senate, the Harvard law professor chaired the Congressional Oversight Panel and helped implement a brand-new government bureau.

Who's flashing this smile?

Elizabeth Warren

congressional oversight panel, consumer financial protection bureau,

A famous golfer, Four-time Masters winner Elin
The clues: The four-time Masters champion hasn't won a tournament since his infidelity scandal broke in 2009.